Dimethylformamide → HCID 11172502, compound

HRID 2254202Notes

Reaction equation

HRID 2254202 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[CH:12](N(CC)C(C)C)(C)C.[CH3:21][O:22][CH2:23]Cl.CN(C)[CH:27]=[O:28]>>[CH3:21][O:22][CH2:23][O:1][C:2]1[CH:7]=[C:6]([O:8][CH2:12][O:28][CH3:27])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 69902',4'-DihydroxyacetophenoneHCID 7864Chloromethyl Methyl EtherHCID 81531Diisopropylethylamine

Product 1

HCID 11172502HCID 11172502, compoundYield 98.3%

Conditions

Temperature
0 °C

Procedure

In 3 ml of dimethylformamide was dissolved 456 mg of 2',4'-dihydroxyacetophenone, and the solution was cooled to 0° C. and 1.73 ml of N,N-diisopropylethylamine was added to the solution. Then, 0.61 ml of chloromethyl methyl ether was added to the mixture and reaction was carried out for 18 hours with stirring. After the reaction, the reaction mixture was poured in ice water and extracted with ethyl acetate. The organic layer was washed with water, dried with anhydrous sodium sulfate and filtered. The solvent was removed from the filtrate by distillation to obtain 707.9 mg (yield=98.3%) of 2',4'-bis(methoxymethoxy)acetophenone in the form of a colorless transparent liquid.

Workup

  1. customAfter the reaction
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed from the filtrate by distillation

Sources & evidence

ORD record
ord-eb370d06222d4760ac2483187f486224
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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